But that might change this year, as Angelo — former Bears general manager who sacrificed two first-round picks, a third-round pick, a fifth-round pick, and quarterback Kyle Orton to acquire Cutler from Denver in 2009 — believes the Bears quarterback is in position to have his best season yet.

“The pressure’s off now. He’s got his contract,” Angelo said in an interview with 87.7 FM The Game. “In all likelihood it’s going to be his last big contract, and he’s firmly entrenched as the starter and he knows what he has to do. I think he’s going to have an outstanding year."

Under one condition.

"The biggest thing right now is just staying healthy," Angelo said of Cutler. "If he stays healthy, the sky's the limit for the team."

In his first season under Marc Trestman's offense, Cutler was posting career numbers before injuries haulted that pace. And Angelo expects him to continue that success.

"It’s a great offense, great personnel around him," he said. "And he’s very, very comfortable now going into his second year [in Trestman’s offense]."

Obviously, some may argue Cutler's $126-million contract will add more pressure to a team that feels they're ready to win now, or perhaps believe Cutler may be content now that he cashed in on a long-term deal. But Angelo believes the Bears confirming its commitment to Cutler — by rewarding him with a seven-year deal — will lead to a more composed and confident quarterback.

“Every quarterback who’s starting in the National Football League feels the pressure to win and to take his team to the next level. That’s a given. So that’s always been there. The pressure I’m alluding to is that he now has the full commitment of the organization, of the coaching staff, etc. Now he’s in a comfort level, and that’s a big weight on players as they go through their process with a team. ... I think you’re going to see a player that now feels totally committed because he feels a total commitment from the organization.”